Marketing Headhunting Veteran Reveals One of His Favorite Interview Questions for Executive Candidates

Ensure a Better Hire. Get Interview 20 Questions You MUST Ask Your Next Marketing Executive Now!

Interviewing marketing leaders is both an art and a science–and important ones at that. A thorough and effective interview strategy is essential to hiring successful marketing leaders who are suited for your company’s culture and needs. And at a time when marketing has never been more important for guiding the business forward toward growth, you can’t afford to make the wrong hire.

Of course, making the most of an interview with a marketing executive candidate means asking the right questions. If you bring generic, stale questions in, you can expect generic, stale answers that don’t offer meaningful vision into your candidates’ qualifications. But thoughtful, directed questions can make all the difference in understanding the candidate and their qualification for your open leadership position.

The questions you ask can and should be customized depending on your business and the role. But there are a few standard conversations you can have with any candidate for any marketing executive job that will be almost universally fruitful.

One of my favorites is: “How long will you fail at this job before you succeed?” Here’s why:

Mindset Insights

What I like about this question as a marketing headhunter is that it provides insights on so many aspects of the candidate’s character and qualifications:

what they think the learning curve is for the job; how big of a personal and professional challenge it will be for them

what they think about their comfort and familiarity with your industry and market

how well they get along with others, establish themselves as a leader and integrate into a senior management team

their ability to plan and outline a schedule for success and hold themselves accountable

their judgement of your organization’s culture and workplace environment, and how well suited they are for it

Those are difficult answers to get without asking your candidate directly, and sometimes direct questions won’t instigate the most useful answers.

No Marketing PhD Required

One of the most common problems that occurs when businesses recruit a new marketing leader is that the people responsible for recruiting and interviewing them aren’t marketing experts themselves. It’s the number one reason why marketing executive searches fail.

Marketing is changing at a constantly accelerating pace, evolving an increasingly multifaceted technical and digital discipline. If you’re not a dedicated expert, you’ll have a hard time asking targeted questions to an experienced marketing executive on their experience, skills, and strategy–especially if you’re engaged in a high-level digital marketing executive search.

Part of the beauty of this question is that anyone in the organization can get a lot out of the answers. CEOs, HR representatives, Sales executives and more who frequently find themselves on marketing executive interview panels can discuss the topic with candidates without getting lost in advanced marketing terminology and concepts.

What to Look For

Like most good interview questions, there’s no single universally best answer you should be looking for.

One major factor to consider is the situation your business is in. If this is an especially urgent hire designed to address an immediate business growth crisis, then you obviously don’t want to hear from a candidate that their integration will take an extended period. On the other hand, if you’re in a relatively stable position then you should be more open to great candidates who might need a little more time to get fully onboard.

But in general, it’s best to watch out for a couple of answers that should send up some red flags in your head.

The first is the professional who envisions an unrealistically short timeline of just a few days or weeks or dismisses the concern as unimportant. This indicates that the candidate is either overconfident, has low definitions of success, or doesn’t understand what success looks like in that position. If your marketing problems are simple enough that a new executive will be able to start delivering ROI on day 1, then they’re probably not even worthy of a new hire.

The second is the candidate who is unwilling to commit to any sort of timelines. Some people may be hesitant to suggest even a rough estimate, citing too many unknown variables or a reluctance to be held to a figure so early in the process. This indicates that they’re not confident in their ability to step into a new environment and make a difference, or don’t have a plan to integrate themselves into your teams, systems and culture.

Rounding out the Interview

This is one of my favorite questions; but it’s far from being my only go-to. There are many I like to use depending on the situation. You can find this and 19 more interview questions carefully designed by marketing headhunters on this checklist we made. Check it out; you can download it now for free!